Perfect Anniversary Journeys
Couples are celebrating milestones differently, through adventure and discovery.
As millennials and Gen Xers hit major milestones in their relationships, they are redefining the ways of what a romantic escape should look like. The all-inclusive beach resort and overwater villa are no longer the go-to’s and they don’t necessarily satisfy a generation that values meaning over luxury. Instead, couples are seeking itineraries and destinations that challenge them, push their boundaries, transform them, and bring them closer together through shared experiences.
Over the past year, as a luxury travel consultant, I’ve designed more than 10 anniversary journeys that defy traditional expectations. None of them featured champagne by an infinity pool or floating breakfasts or towel swans, I can assure you. Coincidentally, every couple asked for three things:
A challenge they could do together
Dining experiences that surprised the senses - but weren’t tasting menus
Some elements of complete privacy, both in accommodation and guiding, so they could connect uninterrupted
Below are three extraordinary anniversary journeys inspired by these real itineraries, each crafted for couples seeking adventure, intimacy, and renewal in 2026.
Journey 1: Culture, History & Barrier Reefs in Guatemala & Belize
Begin in Antigua, Guatemala, a cobblestoned heritage town framed by volcanoes. Craft jade jewelry with local artisans, then ascend Pacaya Volcano with an expert guide to watch lava flow against the night sky. Fly by helicopter to Lake Atitlán, landing at a majorelle-blue villa overlooking the sacred lake ringed by indigenous villages famed for their UNESCO-recognized weaving traditions. Continue north to the lush Petén jungle to explore Tikal’s towering ruins and hidden pyramids overtaken by vines. Cross into Belize to trek through the Mountain Pine Ridge forest, canoe into a skull-lined cave, and end your journey on a private island in the Barrier Reef. Here, days unfold between snorkeling in the Blue Hole, open-air cinema nights under the stars, and complete seclusion.
Journey 2: Twin Island Trek in Madeira & The Azores, Portugal
For couples who think they’ve already “done” Portugal, the islands of Madeira and the Azores offer a new dimension of wonder, just a direct flight away from New York. In Madeira, stay in a botanical garden estate once owned by a Scottish lord. Hike through the misty forests of Fanal, take a private yacht to spot sperm whales and playful dolphins, and toast to each other with a private tasting of Madeira wines atop a historic tower overlooking Funchal. Wake early to watch the sunrise above the clouds before descending to breakfast among waterfalls and wildflowers. Then fly to São Miguel in the Azores for an immersion in raw nature: crater lakes, mountain biking trails, whale watching, and off-road adventures to the volcanic Sete Cidades.
Journey 3: Arctic Intimacy – Swimming with Orcas in Norway
In Norway, head north to the Arctic Circle in Tromsø for one of the world’s most moving wildlife encounters. Spend your days aboard a small expedition yacht, gliding through the icy fjords in pursuit of orcas and humpback whales during the Arctic herring migration. Don a drysuit and slip into the freezing water beside these majestic creatures, guided by marine experts. Evenings are spent warming up in a private glass-fronted cabin, sharing candlelit dinners while the Northern Lights flicker above. It’s an anniversary celebration that redefines connection, both with nature and with each other.
Interested in an Anniversary Trip?
Book a bespoke anniversary trip with Sarah Casewit. Send in your trip request and I’ll be happy to design your bespoke adventure.
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